It needn't have ended this way for Conrad Black, sentenced yesterday to 6 1/2 years of jail time and fined $125,000 (U.S.) for defrauding his own flagship company and obstructing justice.

It needn't have ended this way for Conrad Black, sentenced yesterday to 6 1/2 years of jail time and fined $125,000 (U.S.) for defrauding his own flagship company and obstructing justice.

If only Conrad Black's father hadn't crossed paths with E.P. Taylor, the most celebrated Canadian tycoon of the 1950s. More than anyone, it was George Black who transformed Taylor's motley collection of beer brands (Red Cap, Dow, Black Label) into a Canadian Breweries that led the world in suds sales.

Then, in a spasm of ingratitude, "Excess Profits" Taylor abruptly shoved George Black into retirement – fired him, in effect. George Black would spend the rest of his days tutoring his younger son on the inherent treachery of business and the virtues of paranoia in dealing with the rogues who populate the world of commerce.

If only George Black had been less sympathetic when Con was caught stealing exam papers at Upper Canada College, warning him of the severe consequences of theft rather than promptly beseeching another posh boarding school to take him in. (Black was soon expelled from that school, also, for insubordinate behaviour.)

If only Conrad Black had followed his muse, confining himself to his true calling as a journalist (an exclusive interview with then-South Vietnamese president Nguyen Van Thieu landed Black's byline on the front pages of dailies worldwide) and historian (Black's first doorstopper, a biography of Maurice Duplessis, was published when its author was 32).

If only brothers Conrad and Montegu Black had placed their $7 million inheritance with a professional trustee. Instead, they sought revenge on their late father's behalf by storming the barricades of Taylor's creaky Argus Corp. conglomerate. They then gave a very public demonstration of their lack of business acumen, presiding over the decline of Argus holdings Massey-Ferguson Ltd. and Dominion Stores Ltd., and failing to honour promises of imminent turnarounds that came to be viewed as disingenuous.

If only Black had taken the full measure of Rupert Murdoch's habitual persistence, grasping that the price war launched by Murdoch's The Times of London was not a passing migraine for Black's rival Daily Telegraph, and had the potential to become a drawn-out nightmare that would drain Black's empire of cash flow.

If only Black wasn't so quick to detect libellous intent in references to himself, he would not have created the "libel chill" that foreclosed opportunities for Black's firms to abstain from dodgy dealings brought to light, and which culminated in his criminal prosecution.

If only Black had resisted the vainglorious status as a peer of the British realm, necessitating the surrender of his Canadian citizenship, he would now, like fellow Hollinger felon David Radler, stand a chance of serving his jail time in Canada, where prison conditions are safer than in any of the U.S. prisons to which he will be assigned.

If only he had chosen differently than Barbara Amiel, whose extravagant tastes drew the attention of aggrieved shareholders. Worse, she reinforced Black's already unhealthy sense of entitlement and victimhood.

If only Black hadn't dismayed Chicago judge Amy St. Eve during her sentencing deliberations by spouting off that the U.S. criminal justice system is "essentially a substitute for a wealth distribution policy." That's a fitting description, in the minds of wrathful minority investors in Black's companies, of the pattern by which Black and his cronies seemed to profit from each new Hollinger restructuring while they waited endlessly for a half-decent return on their investment, and eventually called the cops.

If only.

But then he wouldn't be Conrad Black.

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